"Turning the calendar to October can only mean one thing: It’s time for my annual Gilmore Girls rewatch. As much as I love the show for its beautiful, small-town scenery and ever-changing love stories, I can’t help but get excited for the characters’ early-2000s style, too. Although they’re mother and daughter, Lorelai Gilmore and Rory are incredibly different—and that’s especially true in the style department.
Through the seven seasons of Gilmore Girls, we get to know Rory’s preppy, put-together style contrasted with her mom’s colorful, loud, eclectic outfit choices. While the show’s costumes are undeniably nostalgic (you can definitely tell the show aired from 2000-2007), I recently got myself thinking about what Rory and Lorelai Gilmore would wear if the show aired in fall 2024.
These are six outfits I think the leading ladies of Gilmore Girls would be excited to wear during fall 2024.
For a Bit of Light After-School Reading
Sweater (Alternate Option) | Tote | Jeans | Sunglasses | Belt | Clogs | Socks
Rory’s iconic cable-knit sweater moment actually doesn’t need much altering to work in 2024. She’d cozy up under her favorite tree (before being spotted by Dean) in the same oversized knit that she did in the early aughts, but we think this time, she’d opt for Birkenstock clogs instead of her go-to converse. She’d also update her black backpack (later switched for her infamous yellow backpack) for a practical, carry-all tote bag that’s perfect for throwing over her shoulder and heading out the door.
For Breakfast at Luke’s
Jacket | Sweater (Plus) | Bag | Jeans | Sunglasses | Boots
Lorelai Gilmore was known for a funky sweater (and an insane amount of graphic tees), and she never was afraid to rock one that was, ahem… a little out of the box. We think she’d upgrade her pink dog sweater (could this have been a foreshadowing of Paul Anka?) for this year’s Ralph Lauren version, but she’d make it feel a bit more eclectic through styling. She’d opt for vintage knee-high boots (that she’s had in the back of her closet for 20 years, of course), a leather jacket, and a printed, statement-making bag.
For the First Day at Yale Daily News
Socks | Loafers | Tote | Sweater Tee (Plus) | Jeans
Rory’s style really started to transform at Yale and after graduation (dare we say that she may have been inspired by her grandmother, Emily Gilmore?). Each of the pieces in this outfit—a sweater tee, dark-wash denim, penny loafers—are true to Rory’s classic style. Together, they create a sophisticated outfit that’s worthy of pairing with a pink ostrich Birkin bag (IYKYK).
For a Charity Picnic Basket Auction
Jacket | Belt | Sweater (Plus) | Jeans | Bag | Ballet Flats
We know Lorelai has a thing for shoes (I’m still envious of her boot collection), and she’d love pattern mixing by adding a pair of leopard print ballet flats to her iconic collection. She’d also be a fan of this fall’s barn jacket trend—especially a cropped one, like this option from J.Crew. Not one to go for an all-neutral look, she’d go for an unexpected color combination of navy and cherry red to make this outfit a little more interesting.
For a Day of Window Shopping
Boots | Sweater | Skirt (Plus) | Jacket (Plus) | Belt
Rory might have been onto something the day she decided to go window shopping with Lorelai in a camel-colored leather jacket and a gray mini skirt. This outfit can be modernized by pairing a brown leather jacket with a pleated skort, crewneck sweater, and knee-high boots. The varying neutrals in the original outfit helped to give the look some contrast, which is the case here, too. Sorry Rory, but the fishnets did need to go.
For Date Night at the Black-White-Read Bookstore
Knee-High Boots | Sweater | Mini Skirt (Plus) | Bag | Bracelet
When I first saw this sweater, my mind immediately went to Lorelai Gilmore. With stripes in unexpected colors, it would be a staple in her collection of eclectic knitwear. I think she’d style it for a date night watching Pippi Longstocking at the Black-White-Read Bookstore with a mini skirt, knee-high boots, and a red bag for a fun, autumnal outfit that screams “Lorelai.”
Caitlyn Fitzpatrick, Contributing Sex & Relationships Writer
Caitlyn is a New Jersey native and has been a professional writer and editor since 2014. She’s currently a senior editor at Trusted Media Brands, where she edits commerce content for Reader’s Digest, Taste of Home, and Family Handyman. In addition to The Everygirl, Caitlyn’s work can be found in Betches, WhatToWatch.com POPSUGAR, InStyle, StyleCaster, Best Products, Popular Mechanics, and more.
Madeline Galassi, Senior Fashion & Beauty Editor
Madeline Galassi is the Fashion & Beauty Editor at The Everygirl, where she oversees the fashion and beauty categories of the site. She brainstorms, writes, and edits stories across a broad range of topics including trend reports, product reviews, celebrity style, and more. She’s always keeping a pulse on the latest trends to create timely, exciting content for our readers.